Process for the manufacture of acid esters of cyclical terpene alcohols.



UNITED STATES PATENT OFFICE.

OTTO ZEITSCHEL, OF HAMBURG, GERMANY.-

PROCESS FOR THE MANUIAOTUBE OF.ACID ESTERS OF CYOLIOAL TERPENE ALOOHOLS.

Specification of Letters Patent.

Patented Dec. 29, 1908.-

Application filed July 80, 1907. Serial 1501886358.

To all whom it may concern:

Be it known that '1, vQcr'ro ZnrrsoHnL, a subject of the German Emperor,and a resldent of Hamburg, new and Improved Process for the Mannfactureof Acid Esters of Cyclical Terpene Alcohols, of which the following is aspecification. i v 1 This invention relates to a process for obtaininthe acid esters of the cyclical terpene alcoho s of the formula. C I-IOH from tor penes, such as pinene, camphene, fenchene, or from othermaterials containing said substances, such as oil of turpentine.

In carrying out my invention, the above materials are mixed with organicacids, (such as acetic acid, valerianic acid, butyric acid, palmiticacid, benzolc acid, phthalic acid, salicordin cylic acid, cinnamicacid), m approximately molecular proportions, and then the mixture isheated to a tem erature of about 200 0.,- such temperature hours, sayfive hours. The product is cooled, any remaining acid is removed inmanner acto the kind used, and the result' neutra product is subjectedto fractiona distillation, so as to separate the pure acid ester.

My improved process may be carried out as follows:

1. 136 kg. (1 mol.) of French tu ntine oil are heated with 60 kg. aceticacid lmol.) in autoclaves to a temperature of 200 C.

and maintained at, that temperature for Germany, have invented a' eingmaintained for a few.

about 5 hours. After cooling, the excess of acid is removed and theneutral product of reaction is submitted to fractional distillation. Ifthe-process is properly carried out the resinification is very cent andabout -1015% camphene (including fenchene), 30-40% limonene (dipentene)and about 40% acetates of borneol (including f enchylacetate) areobtained.

2. 136 kg. (1 molecule) turpentine oil or the corresponding molecularquantity of a material containing cam hene or fenchene are heated with100 kg. about lmolecular proportion) of benzoic acid in autoclaves toabout 200 O. f d maintainedat that temperature for about 5 hours. Aftercooling, the excess of acid is removed and the esters which are noteasily volatile, are separated,

by refining with steam from the volatile terenes which, in their turn,"are subjected toactional distillation. The products stance formanufacturing Borneo oils. and cam hor or for perfumery purposes.

e course of reaction for upmene is illusrm a,

trated in the following fo in which R stands for an acid radical. Ifthus, the radical C C0, of acetic acid is substituted for R, the ormulaillustrates the reaction-oi the first example. If the radical C,H CO, ofbenzoic acid is substituted for R, the reaction of the second example isillustrated by the formula:

. obtained can be used for inon CH I \OH: cm-c -cu I on on on on 0H3 or;m \J c b c z n II 111 da on 0H /CH\ H 011 \CH2 011 on on, I on, on 0 CHJ Lo o-om H I 011 -cH,,] 3

B on H c on c \c 2 c R c \R V m (is c413 Terpinylester BomylesterFenchylester ucm cm If cin crn on t c I l al! Limonene What I claim is:product to fractional distillation, substan- 10 A process for producingacid esters of c clical tergsne alcohols of the formula S1gned me atHamburg, Germany this CZJI-II OH, w 'clasconsists in ter ienes 15th dayoi July 1907. 5 wit organic aci in a proximate y mo ecu-' larproportions, heating the mixture for OTTO ZEITSCHEL' about five hours toabout 200 0., cooling the I Witnesses tially as s ecified.

mixture, removing the excess of acid to ob AUGUST WENK, tain'a neutralproduct, and subjecting said ERNEST H. L. MUMMENHOFF.

